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Showing metabocard for 4-Methylumbelliferone (HMDB0059622)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2023-02-21 17:29:09 UTC
HMDB IDHMDB0059622
Secondary Accession Numbers
  • HMDB59622
Metabolite Identification
Common Name4-Methylumbelliferone
Description4-Methylumbelliferone, also known as hymecromone or 4-MU, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. 4-Methylumbelliferone is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-methylumbelliferone is a substrate for: Liver carboxylesterase 1, Cocaine esterase, and S-formylglutathione hydrolase.
Structure
Data?1677000549
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0059622 (4-Methylumbelliferone)

4MU
  Mrv0541 02241213122D          

 13 14  0  0  0  0            999 V2000
   -0.7173   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4317   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4317    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406    0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117    0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -1.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173    0.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3 12  2  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
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3D MOL for HMDB0059622 (4-Methylumbelliferone)

HMDB0059622
     RDKit          3D
4-Methylumbelliferone
 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.2486   -1.4823    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5472   -0.1960    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    0.9749    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5859    2.1510   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    3.2188    0.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2709    2.1812   -0.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    1.0883   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    1.1383   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -0.0002   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1163   -0.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -1.2221   -0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036   -1.2904   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619   -0.1435   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2403   -1.8536    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -1.3436   -0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338   -2.2375   -0.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3851    0.9674    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    2.1080   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625    0.1777    0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972   -2.1060   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -2.2468    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13  2  1  0
 13  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  8 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
M  END
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3D SDF for HMDB0059622 (4-Methylumbelliferone)

4MU
  Mrv0541 02241213122D          

 13 14  0  0  0  0            999 V2000
   -0.7173   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4317   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4317    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406    0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117    0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -1.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173    0.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3 12  2  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059622

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)OC2=C1C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3

> <INCHI_KEY>
HSHNITRMYYLLCV-UHFFFAOYSA-N

> <FORMULA>
C10H8O3

> <MOLECULAR_WEIGHT>
176.1687

> <EXACT_MASS>
176.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.41709365802293

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-4-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
1.7791888986666664

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.800072891159978

> <JCHEM_PKA_STRONGEST_BASIC>
-6.950886758662731

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
47.81150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methylumbelliferone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0059622 (4-Methylumbelliferone)

HMDB0059622
     RDKit          3D
4-Methylumbelliferone
 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.2486   -1.4823    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5472   -0.1960    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    0.9749    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5859    2.1510   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    3.2188    0.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2709    2.1812   -0.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    1.0883   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    1.1383   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -0.0002   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1163   -0.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897   -1.2221   -0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036   -1.2904   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1619   -0.1435   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2403   -1.8536    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -1.3436   -0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338   -2.2375   -0.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3851    0.9674    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    2.1080   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625    0.1777    0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972   -2.1060   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -2.2468    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13  2  1  0
 13  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  8 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
M  END
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PDB for HMDB0059622 (4-Methylumbelliferone)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4MU                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.339  -1.594   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.673  -0.824   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.673   0.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.662   0.716   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.662  -0.824   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.329  -1.594   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.996   1.486   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.329   1.486   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.329  -3.134   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.005  -0.824   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.005   0.716   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.339   1.486   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.006   1.486   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2   12   13                                                  
CONECT    4    5    7    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    9   10                                                  
CONECT    7    4                                                            
CONECT    8    4   11                                                       
CONECT    9    6                                                            
CONECT   10    1    6   11                                                  
CONECT   11    8   10   12                                                  
CONECT   12    3   11                                                       
CONECT   13    3                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0059622 (4-Methylumbelliferone)

COMPND    HMDB0059622
HETATM    1  C1  UNL     1      -2.249  -1.482   0.117  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.547  -0.196   0.049  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.304   0.975   0.066  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.586   2.151  -0.001  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.266   3.219   0.014  1.00  0.00           O  
HETATM    6  O2  UNL     1      -0.271   2.181  -0.075  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.457   1.088  -0.091  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.847   1.138  -0.170  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.619  -0.000  -0.188  1.00  0.00           C  
HETATM   10  O3  UNL     1       4.015   0.116  -0.269  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.990  -1.222  -0.126  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.604  -1.290  -0.047  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.162  -0.143  -0.030  1.00  0.00           C  
HETATM   14  H1  UNL     1      -2.240  -1.854   1.167  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.306  -1.344  -0.190  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.834  -2.237  -0.591  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.385   0.967   0.126  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.344   2.108  -0.219  1.00  0.00           H  
HETATM   19  H6  UNL     1       4.563   0.178   0.599  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.597  -2.106  -0.141  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.116  -2.247   0.001  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3   13
CONECT    3    4   17
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   18
CONECT    9   10   11   11
CONECT   10   19
CONECT   11   12   20
CONECT   12   13   13   21
END
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SMILES for HMDB0059622 (4-Methylumbelliferone)

CC1=CC(=O)OC2=C1C=CC(O)=C2
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INCHI for HMDB0059622 (4-Methylumbelliferone)

InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-Methyl-7-hydroxycoumarinChEBI
4-MUChEBI
7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyranChEBI
7-Hydroxy-4-methyl-2-oxo-3-chromeneChEBI
7-Hydroxy-4-methyl-2H-1-benzopyran-2-oneChEBI
7-Hydroxy-4-methylcoumarinChEBI
beta-MethylumbelliferoneChEBI
HimecromonaChEBI
HymecromoneChEBI
HymecromonumChEBI
ImecromoneChEBI
CantabilineKegg
b-MethylumbelliferoneGenerator
Β-methylumbelliferoneGenerator
4 MethylumbelliferoneHMDB
MethylumbelliferoneHMDB
ResocyanineHMDB
7-Hydroxy-4-methyl-coumarinHMDB
MendiaxonHMDB
7 Hydroxy 4 methyl coumarinHMDB
CholestilHMDB
4-MethylumbelliferoneMeSH
Chemical FormulaC10H8O3
Average Molecular Weight176.1687
Monoisotopic Molecular Weight176.047344122
IUPAC Name7-hydroxy-4-methyl-2H-chromen-2-one
Traditional Name4-methylumbelliferone
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)OC2=C1C=CC(O)=C2
InChI Identifier
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
InChI KeyHSHNITRMYYLLCV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.99 g/LALOGPS
logP2.19ALOGPS
logP1.78ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.81 m³·mol⁻¹ChemAxon
Polarizability17.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.91231661259
DarkChem[M-H]-134.42831661259
DeepCCS[M+H]+136.4830932474
DeepCCS[M-H]-133.65530932474
DeepCCS[M-2H]-169.84630932474
DeepCCS[M+Na]+145.38430932474
AllCCS[M+H]+134.532859911
AllCCS[M+H-H2O]+129.932859911
AllCCS[M+NH4]+138.832859911
AllCCS[M+Na]+140.032859911
AllCCS[M-H]-134.032859911
AllCCS[M+Na-2H]-134.332859911
AllCCS[M+HCOO]-134.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.4.93 minutes32390414
Predicted by Siyang on May 30, 202211.442 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.22 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1404.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid382.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid148.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid230.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid131.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid470.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid444.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)117.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid923.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid333.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1191.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid303.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid305.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate415.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA276.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water102.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-MethylumbelliferoneCC1=CC(=O)OC2=C1C=CC(O)=C22843.3Standard polar33892256
4-MethylumbelliferoneCC1=CC(=O)OC2=C1C=CC(O)=C21904.8Standard non polar33892256
4-MethylumbelliferoneCC1=CC(=O)OC2=C1C=CC(O)=C22064.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Methylumbelliferone,1TMS,isomer #1CC1=CC(=O)OC2=CC(O[Si](C)(C)C)=CC=C122048.6Semi standard non polar33892256
4-Methylumbelliferone,1TBDMS,isomer #1CC1=CC(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C122299.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone EI-B (Non-derivatized)splash10-002b-3900000000-9efd3962e332f4fe7d262017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone EI-B (Non-derivatized)splash10-002b-6900000000-936015a6cd7badae842d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0f8a-2980000000-3aeee58378773e7d12192017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0ugj-2960000000-f6994262beea96fffc262017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0f89-2960000000-1ab50bc14647991bd5d22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0faj-2970000000-4b2dc64a826d132a7ac22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-9adb76fb1e3b45a0c8842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-4e4875af7ba45d8e6b442017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0ugj-2970000000-884a310f76d9d267a70b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone EI-B (Non-derivatized)splash10-002b-3900000000-9efd3962e332f4fe7d262018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone EI-B (Non-derivatized)splash10-002b-6900000000-936015a6cd7badae842d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0f8a-2980000000-3aeee58378773e7d12192018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0ugj-2960000000-f6994262beea96fffc262018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0f89-2960000000-1ab50bc14647991bd5d22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0faj-2970000000-4b2dc64a826d132a7ac22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-9adb76fb1e3b45a0c8842018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-4e4875af7ba45d8e6b442018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0ugj-2970000000-884a310f76d9d267a70b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylumbelliferone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-0900000000-61e4a7e4dde1895885e12016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylumbelliferone GC-MS (1 TMS) - 70eV, Positivesplash10-00ej-5790000000-01d3673ec552268394fb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylumbelliferone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone ESI-TOF 30V, Negative-QTOFsplash10-00lr-0900000000-3fbf9ca915c0d92b76b82017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone ESI-TOF , Negative-QTOFsplash10-00lr-0900000000-3fbf9ca915c0d92b76b82017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone ESI-TOF 30V, Negative-QTOFsplash10-00lr-0900000000-3fbf9ca915c0d92b76b82017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone ESI-TOF , Negative-QTOFsplash10-004i-0900000000-7310a945d17eac4e20592017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone DI-ESI-qTof , Positive-QTOFsplash10-00b9-0900000000-dbaabe103373f8223a002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone DI-ESI-qTof , Negative-QTOFsplash10-00lr-0900000000-f5b0dc40956eb4d6a0c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-15179f6a234b8a7d3cf62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-4a4f4d19d44ec53053cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , negative-QTOFsplash10-0159-5900000000-67144e5ea0eccd5026332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-afc39113149e898d6ec72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-be2b46a238d108a6f9d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-6e6f0d61b2f7d894a33f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-bb66d78d1350716d53782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone Linear Ion Trap , negative-QTOFsplash10-00e9-0900000000-80bbdd2e5005d9ff91dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone Linear Ion Trap , negative-QTOFsplash10-00e9-0900000000-99219a886e78059019412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-TOF , negative-QTOFsplash10-00lr-0900000000-3fbf9ca915c0d92b76b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , positive-QTOFsplash10-004i-2900000000-4991f1c9aad4efc830aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , positive-QTOFsplash10-004i-2900000000-dde217681388bfa4bc932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-86b0f5bf4b6d213d6c7d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 10V, Positive-QTOFsplash10-004i-0900000000-8291807d2225eacd271c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 20V, Positive-QTOFsplash10-004i-0900000000-ca6205f9f97f55456bf72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 40V, Positive-QTOFsplash10-002r-4900000000-9f86a6318eefcf9b69ce2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 10V, Negative-QTOFsplash10-004i-0900000000-cc2b1e7f3f612901e8bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 20V, Negative-QTOFsplash10-004i-0900000000-7e08315e76bb28199f322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 40V, Negative-QTOFsplash10-0059-2900000000-8e6be50bdb9190fc6a052016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07118
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444190
KEGG Compound IDC03081
BioCyc IDCPD-182
BiGG IDNot Available
Wikipedia LinkHymecromone
METLIN IDNot Available
PubChem Compound5280567
PDB IDNot Available
ChEBI ID17224
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakamura T, Ishikawa T, Nanashima N, Miura T, Nozaka H, Nakaoka R, Sato T: 4-Methylumbelliferone induces the expression of membrane type 1-matrix metalloproteinase in cultured human skin fibroblasts. Biochem Biophys Res Commun. 2002 Nov 15;298(5):646-50. [PubMed:12419303 ]
  2. Nakamura R, Kuwabara H, Yoneda M, Yoshihara S, Ishikawa T, Miura T, Nozaka H, Nanashima N, Sato T, Nakamura T: Suppression of matrix metalloproteinase-9 by 4-methylumbelliferone. Cell Biol Int. 2007 Sep;31(9):1022-6. Epub 2007 Mar 20. [PubMed:17470403 ]
  3. Saito T, Tamura D, Nakamura T, Makita Y, Ariyama H, Komiyama K, Yoshihara T, Asano R: 4-methylumbelliferone leads to growth arrest and apoptosis in canine mammary tumor cells. Oncol Rep. 2013 Jan;29(1):335-42. doi: 10.3892/or.2012.2100. Epub 2012 Oct 23. [PubMed:23124556 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Methylumbelliferone → 3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails
Enzyme Details
2. Liver carboxylesterase 1
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails
Enzyme Details
3. Cocaine esterase
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular weight:
68898.39
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails
Enzyme Details
4. S-formylglutathione hydrolase
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:
ESD
Uniprot ID:
P10768
Molecular weight:
31462.545
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails